Highly oxygenated polyketides produced by Trichoderma koningiopsis QA-3, an endophytic fungus obtained from the fresh roots of the medicinal plant Artemisia argyi
Highly oxygenated polyketides produced by Trichoderma koningiopsis QA-3, an endophytic fungus obtained from the fresh roots of the medicinal plant Artemisia argyi
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由木霉 QA-3 产生的高氧聚酮化合物，这是一种从药用植物艾叶新鲜根中提取的内生真菌
DOI：
10.1016/j.bioorg.2019.103448
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发表时间：
2020-01-01
影响因子：
5.1
通讯作者：
Wang, Bin-Gui
中科院分区：
文献类型：
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作者：
Shi, Xiao-Shan;Li, Hong-Lei;Wang, Bin-Gui
从著名药用植物艾叶（Artemisia argyi）的根内组织真菌Trichoderma koningiopsis QA-3中分离得到8个新的高氧合真菌多酮，分别为15-羟基-1,4,5,6-四-epi-koninginin G(1)、14-羟基koninginin E(2)、koninginin U(3)、4'-羟基koninginin U(4)、koninginin V(5)、14-酮inginin B(6)、14-羟基koninginin B(7)和7- o -methylkoninginin B(8)，以及6个已知的相关类似物（9-14）。这些化合物都是双环聚酮，其中化合物1在C-5上含有不寻常的半块状部分，化合物2-14在C-1上含有酮基和C-5上的双键(6)。通过光谱分析、x射线晶体衍射、改进Mosher法和ECD计算，确定了新化合物的结构和绝对构型。已知化合物9、10和12的绝对构型首次用x射线晶体衍射测定。对化合物1 ~ 14对人致病菌、海洋源水生细菌和植物病原真菌的抑菌活性进行了评价，化合物1对水生致病菌溶藻弧菌的抑菌活性显著，MIC值为1 μ g/mL，与阳性对照相当。
Eight new highly oxygenated fungal polyketides, namely, 15-hydroxy-1,4,5,6-tetra-epi-koninginin G (1), 14-hydroxykoninginin E (2), koninginin U (3), 4'-hydroxykoninginin U (4), koninginin V (5), 14-ketokoninginin B (6), 14-hydroxykoninginin B (7), and 7-O-methylkoninginin B (8), together with six known related analogues (9-14), were isolated from Trichoderma koningiopsis QA-3, a fungus obtained from the inner root tissue of the well known medicinal plant Artemisia argyi. All these compounds are bicyclic polyketides, with compound 1 contains unusual hemiketal moiety at C-5 and compounds 2-14 having ketone group at C-1 and double bond at C-5(6). The structures and absolute configurations of the new compounds were established by spectroscopic analysis, X-ray crystal diffraction, modified Mosher's method, and ECD calculation. The absolute configurations of the known compounds 9, 10, and 12 were determined by X-ray crystal diffractions for the first time. The antimicrobial activities against human pathogen, marine-derived aquatic bacteria, and plant-pathogenic fungi of compounds 1-14 were evaluated, and compound 1 showed remarkable activity against aquatic pathogen Vibrio alginolyticus with MIC value 1 mu g/mL, which is as active as that of the positive control.